Boulevard of Broken Dreams
by nahsiep
Summary: When 2 broken souls meet, each craves the temporary adventure the other can provide. What happens when the truth comes out and all that's left is heartbreak? AU/AH, Delena story
1. Prologue

Prologue

"You really should give them a hand," I said, smiling coyly at the gorgeous man beside me, looking into his cerulean eyes, "He really looks like he have no idea how to interpret all those obvious signs my friend is giving him!"

Caroline is, at the moment, batting her lashes at the sandy-haired cutie beside her. She is sipping her cocktail in the most ladylike way I've ever seen her, while she bobbed her head up and down, hanging on to the cutie's every word.

"Leave it to my brother to ignore any advances beautiful women have been throwing him," the man beside me quipped, "I swear I thought he was going to enroll himself into a monastary, or worse, come out of his closet!"

"But you, my lovely lady," He turned to me suddenly. "Feel free to come on to me in any way you like. Unlike my brother there with his thick skull, I definitely know how to treat a girl right." He winked.

"Right, and you don't even remember that we have met before!" I laughed. "A kiss say you can't even remember my name, Damon."

"You're on!" Damon furrowed his brows in concentration. God... His eyes are just so captivating and blue. I don't even dare to maintain eye contact for more than 3 seconds. Who knows how long I need to pull myself out of the deep blue ocean of his eyes.

"Amy? Karen? Erm..." His eyes lit up suddenly, like a lightbulb just went off in his mind. "Elly! Right? I know I'm right! Come on, pay up!" He puckered his lips suggestively.

I looked at him, wearing a look of awe and surprise. "Wow! I have to say, a girl really should feel flattered that she's remembered by the great Damon Salvatore."

He looked entirely too pleased with himself. I can see him leaning forward, looking at me expectantly, his blue eyes almost boring into my soul. He closed his eyes and hovered, waiting for me to close the last 2cm of space in between us, when I dodged out of the way at the last minute.

"But nope, no such luck. I guess I'm just not memorable enough."

I smiled and left him standing with his jaw slack and mouth wide open, while I floated away, motioning to Caroline that I'm leaving, and exited the club. 


	2. Chapter 1

My heart is pounding. I have never heard such loud rushing in my ears before, and I am willing to bet 100 bucks that my face is flushing as bright as the tackiest Santa Claus outfit.

Damon Salvatore. Such a sexy name; and boy, the man really precedes the name. With his short, messy charcoal black hair, bright blue eyes, and lean physique, I won't be surprised if he is the subject of many dirty dreams of the general female population.

For just that single moment, I forgot about the troubles that will no doubt surface again come dawn. I guess I should allow myself the indulgence.

When Caroline and I bumped into her old school-mate, Alaric Saltzman, at Lava, the local hippest club, I had no idea I will also be introduced to the man who would plague my dreams for one whole week. I had looked at him with bashful eyes, too shy to even start a conversation. Caroline and Alaric had taken some time to catch up with the latest news and gossip, but I did not even take the chance to say more than the barest hello.

He must have thought that I was the rudest and dumbest girl alive. I thought to myself.

Damon, on the other hand, had no shortage of attention. He was fending off earnest girls the whole night, looking deep in thought as he down glass after glass of bourbon.

I was staring at him like a creepy stalker, as if as long as I look hard enough, I would be able to understand what put a frown to his pretty face. Just when I finally mustered enough courage to approach him, Caroline stood up with a gigantic yawn and announced that we were leaving. I thought I would never see him again.

Until tonight, 1 month later, at the same club. He looked much happier tonight, laughing and joking and winking at every single female around him.

If only I trusted my instincts, kept his damaged look in mind, and stayed far, far away...

What the hell. I thought to myself as she darted out of view and disappeared into the crowd. I could still catch a whiff of shampoo. Something citrusy and fresh. Her smooth and shiny brown locks framing her beautiful face. Bright, dark eyes, peering flirtatiously at me just a second ago as I struggled to recall her name.

And then she's gone. Just like that.

What the hell?

Who is she? How could I forget a girl so beautiful? Or the better question is, how could I have met her, got her name, and not have made a move to know her? And well, know know her (if you catch my drift).

When I finally snapped out of it, it was too late. She has got to be gone by now. I stomped towards my brother, grabbed him aside, and zeroed into the pretty blonde.

"What's her name? Who is she? When have I seen her before? Where does she stay?" I shot question after question, as the blonde held her own, looking nonplussed at my outrage.

"Erm, hello? Do I look like a stupid blonde to you?," she said, just slightly rolling her eyes. "Why would I just randomly give you her details when I barely know you, Damon?"

Wha...? I squinted at the blonde and concentrated. "Have I met you before tonight, too?"

She shot up from her seat, looking offended. "Er, ya! How can you forget not one, but two beautiful ladies you've met barely a month ago? Is your middle name Dory or something?"

"What the hell is a dory?" Caroline crossed her arms and narrowed her brows. "Now, are you going to talk or what?" My patience is wearing dangerously thin.

"No can do, Mr Salvatore. And thanks for spoiling my night." Caroline took off, threading her arm with Stefan's. My brother shot me a "I have no idea what is going on but I'm more interested in the girl"'s look before directing the blonde to God knows where.

Definitely not my night. 


	3. Chapter 2

**Chapter 2**

"Ughhhhh!" I grunted, "Shut up!" My phone rang for the third consecutive time, and much as I tried to ignore it, the noise just wouldn't stop.

I grabbed the offensive object and glared at it. The digits shone brightly in the dark. "Whoever this is, you better have a damn good explanation for calling at three friggin AM!" I almost yelled into the phone.

"YES! I should really give Slater a bonus!" A deep male voice rang out, sounding entirely too happy and enthusiastic for a phonecall that came in the middle of the night.

"Who the hell is Slater, and who is this?" I demanded, losing patience faster than a tornedo destroying houses in its path.

"It's me! I know your name! You are Elena Gilbert, right?" The male voice chirped.

"Pleasure, I'm sure." I bit out, beyond annoyed by now. "Now, this is a little too bright and cheery for such a godforsaken hour, and I need to wake up in 2 hours. I don't associate myself with weirdos who call in the middle of the night and do the happy dance, for that matter. Bye now." I hung up, switched the phone off for good measure, and fell back into bed. I was sure confusion will come in the morning, but that should come when the sky is bright, along with the other human troubles.

The next morning came with relatively little pain, and I almost forgot about that late night phonecall. The screen of my phone gleamed alive just when I was about to take my first gulp of coffee, showing a new message.

_Unknown number: Dawn has broken! Brighter and cheerier, yes?_  
_Me: Huh? Who is this and how did you get my number?_  
_Unknown number: That's for me to know, and for you to..._

Huh. The late night nuisance came back to me with a vengeance. So this is the random person who disturbed my much needed sleep last night. Glancing at the Tag Heuer on my wrist, I decided finding out the identity of this mysterious annoyance is definitely not high on my list.

Ignore it is then.

* * *

"And that was the fifth time you've looked at your phone in the last 30 minutes! What is the matter with you, my dear friend? It is not going to spontaneously explode in your hand, you know." Alaric rambled on while I continued to float towards my private little lala land.

I found her. I actually_ found_ her. That is what I call money well spent. Slater may charge for an arm and a leg, but he has proven to me time and again that he is the top of the business. Just a description of the mysterious chestnut-haired girl and her friend, Carol or Carrey whatshername, and I got my answer in 48 hours.

I glanced at my phone again. _Why is she not replying?_ I'll admit, calling her immediately after getting her number is not my M.O., and maybe even slightly overzealous, but she has strangely been a part of my every thought since that night. What is it about her? Why can't I forget her big brown eyes, lashes fluttering flirtatiously at me, long chocolate locks... hell, I can even remember her citrus shampoo.

"Hello? Earth to Damon!" Alaric snapped his fingers. "Who are you and what have to done to Damon Salvatore?" He demanded.

"What is it, buddy?" I snapped. "A man can't even have some time to his own thoughts now?"

"Not when we are talking about a 20 million deal, he can't." Alaric suddenly faced me, inching closer and started examining my face closely.

"Sorry dude, I know your boundless love for me, but I just don't swing that way." I said, slowly rolling my chair backwards as he came closer over my desk.

"It's a girl, isn't it? Another one of your conquest? A notch on the your bedpost? Are you trying to set a new record?"

"Woah, woah, man." I felt the wheels of my chair hit the floor-to-ceiling windows behind me. "Enough, I can answer those questions without you literally breathing down my neck!"

Alaric stood up straight and crossed his arms. "So? What is it?"

"Well, there's this girl..."

"I knew it!" Alaric raised his left brow and looked at me accusingly. "Don't you ever get tired of this? I can just imagine what _she_ will say to that. You know she..."

"Don't you dare breath even the first syllabus of her name." I bit out. "This conversation is over."

I turned my chair abruptly and faced the view the room offered. The whole financial district of New York City, on display right in front of me from my 47th storey office. Being rich and powerful in the real estate business has its perks.

I rotated my chair back to face the room when I heard the small click of the closing of my door. I glanced around, taking in the dark grey wallpaper, the 6 LCD screens on one of the walls, 4 of which display the latest stock and property market news, 1 tuned permanently to the city's news channel, and 1 showing the video the surveillance camera has captured outside my room.

It's almost amusing how my mood can be dampened by a single insinuation of _her_. I heaved out a sigh, and dialed the all-too-familiar number.

"Hey." I said softly into the phone. "Yes, I'm in the office... I'll see you tonight. Don't wait up."


	4. Chapter 3

**Chapter 3**

I nervously smooth out the slight crinkles on my lavender Ferragamo blouse, and cross my hands daintily on my lap. 25 years worth of facing the man, and I still get antsy and cringe whenever the mere thought of him rolls into my mind.

"Miss Gilbert? He's ready to see you. This way please." The red-haired girl, who couldn't be more than 22 years old, gestures to the door. I eye her short and tight bandage skirt, almost see-through blouse and sky high heels. _Must be his flavour of the month._

Squashing that bitter thought, I square my shoulders, and approach the dark wood door. The silver name plate shines in the harsh fluorescent lighting, polished meticulously by one of the 60 cleaning staff peppering the premises every morning._ Mr Grayson Gilbert. CEO, G Enterprises._

I knock gingerly, and force my feet through the door.

"Finally. Does your indiscretions know no bounds?" A booming voice rings out. "I asked for you 45 minutes ago! Took your own sweet time, didn't you?"

I pause at the door, facing the divider screen in front of me, nervously biting my lips. The feeling of dread threatens to take over me while I mentally prepare myself for what is going to happen once I step into his view.

"By all means, move at a glacial pace. You know how that absolutely _thrills_ me." My dad barks. "I do seem to have all the time in the world, don't I?"

I hurry to the other side of the divider, and present myself in front of him. A giant of a man, my dad stands at 1.9 meters tall. Despite being sixty-five, he makes up for his age with his muscular physique and full crown of hair, nary a white strand or bald patch in sight. The only tell is the 2 deep frown lines which have been permanently carved in between his brows.

I can still remember the time when he wore a pleasant smile on his face, welcoming me into his warm hug every day when he came home from work. A long, faraway memory. I can't help but feel a tinge of sadness at the thought.

"So." His loud voice pulls me abruptly back to the present. I put on my game face and look at him, shuddering inwardly while bracing myself for the cruel words that will soon come. He hunches over the mountain of papers that adorns his desk, squinting at the words, and examines something on his computer screen closely.

"Have you managed to settle the deal I told you about 2 days ago?" He peers over his glasses slightly, momentarily breaking his vision from the thick stack of paper he clenches tightly in his hand. Of course he won't bother with any niceties. "I told you to update me with progress every day, haven't I? Why is it so hard for you to obey such simple instructions?"

I take a deep, silent breath, and force myself to calm down. No good will come if I butt heads directly with the man. I am stubborn, but I am not stupid.

"I am still trying to get close to him, Father." I speak slowly, afraid that a single wrong word will set him off. No one has ever experienced the full extent of his quick and ferocious temper as much as I, since almost everything I do seem to give him reasons to shout at me on an almost unerring daily basis. I definitely plan to prolong the temporary calm of the moment as much as possible. "But he is a very... friendly man. I need more time to get his attention."

"You are useless!" He slaps his hand loudly on his table. Some documents fall from the mountain of papers and litter the floor. "How is it that I have such a worthless daughter who cannot even contribute a teeny tiny amount to the business? And you wonder why I have not yet formally introduced you to the society even though you have certainly come of age." He stands up and stomps in front of me. "I would really like to know what I have done in my previous life to deserve a child as ungrateful and entitled as you."

I keep my eyes on him, tears edging the corners of my eyes, threatening to spill over. No. I will not let him have that satisfaction.

"Why don't you send your little slut currently perched outside your door to do it then?" I retort, unable to reign in my temper anymore. If someone need proof of my genetic relations to the man, our tempers would be the inarguable evidence. "I'm sure she will perform much better than me, in all manners of the word, as I'm sure you already know."

I turn and start to march out of the room, when I am pulled back by a firm grip on my arm. _Slap!_ My cheek instantly flare up in a bright shade of crimson as I let out a loud gasp.

"How dare you speak to me this way! Who do you think you are?" My father glared menacingly at me. I am sure he will not hesitate to whip out a second slap, gauging by the level of his anger. "I am your FATHER. You'll do well to show me some respect!"

I scowl at him, reflecting almost the same amount of disdain he is wearing on his face. If the tension in the air is not so suffocating, the similarities in our expressions would almost be comical.

"Respect, like trust, is earned. I can't just magically hand it over. But I'm sure this is a concept you will never comprehend."

I spin on my heels, slightly pleased to get in the last word, and rush out as fast as I can, cradling my sore cheek with my right hand.

* * *

I step eagerly into Lava, beelining for the bar. What a serious, no nonsense, crappy day. My pounding headache forces me to rub the bridge of my nose every few steps, no thanks to the impossibly crowded spreadsheet I was staring at all day. None of my calculations made sense, and I blame the non-reply I got from Elena. I refuse to swallow my dignity and send her a message again. I generally hate persistent women who couldn't take a hint, and God forbid I turn into a male version myself.

Elena. What a pretty name. She seems to hover around my every thought, rendering me completely unable to concentrate as I plough through my annual investors' report these past few days. Damn her and the disease she infected me with. I certainly hope this is just a fad, a temporary insanity on my part.

I down my bourbon in 2 big gulps. Maybe the memory of her will fade in a few days. _Who am I kidding._ It had been a grand total of 10 days since I last saw her, and I still find myself glancing anxiously at my phone every few minutes. I brought it with me everywhere, even to the loo. _I am acting like a lovesick puppy_, I suddenly realise.

What the hell is wrong with me?

I motion to the bartender to bring me another double shot, preparing to cradle my poison and hide in the dark shadows of the VIP lounge while I drink away the images of the long haired beauty.

Sipping the caramel-colored potion wistfully, I ponder calling some girl for a much-needed distraction. Just when I am scrolling through my phone list, I notice a heady fragrance. I sniff.

Hell, I'm smelling her scent around me now? I swear I'm turning psycho!

I look up from my drink and narrow my eyes. Matthew Donovan, the son of D & M Inc, one of my fiercest competitors, is strutting purposely towards my table. A girl with long chestnut brown hair, large doe eyes and carrying the unmistakable smell of citrus shampoo clings on his arm. The girl whom I have been thinking of for the past almost 2 weeks. The girl who ignored my messages. Now I know why.

"Salvatore! Fancy seeing you here! Have your falling sales finally driven you to drown your sorrows alone?" Matt sneers, holding Elena around her waist possessively. I thought I saw the slightest flinch on her face, but it disappeared as fast as it happened. "Have you met the lovely Elena Gilbert, golden princess of G Enterprises? Isn't she gorgeous?"

He smirks at her as if she is one of his latest addition to his obscene vintage cars collection. I could feel him trying to detect a hint of envy from me, as he gauges my reaction from the corner of his eyes.

Besides being business competitors, Matt, having almost as impressive a track record as me in charming members of the female gender, has listed me as one of his challengers in the dating field. He is constantly trying to shove his latest conquest into my face, in a truly crass "my girl is better than yours" fashion. Too bad I don't give a shit.

Until now. I watch her as she looks at me with slight panic in her eyes. "Miss Gilbert. Pleasure to meet you." I struggle to keep my voice and face cold and detached. She extends her hand and smiles timidly, "Pleasure to meet you too, Mr Salvatore."

Gone is the witty girl who left such a deep impression on me the other night. No radiating confidence, no playful expression in her eyes, no smart retorts. The girl standing in front of me is like her weaker twin, one who is meek, unable to make her own decisions, and only speaks when spoken to.

Unexplained fury rose inside of me. I have no idea why I feel so disgusted and irritated by Elena at this moment. "Excuse me, I have somewhere I need to be. Enjoy your night." I bang my glass on the table and storm out of the club, every step making me angrier and angrier.

Is the girl I have been thinking about just a mirage? A figment of my own imagination? I kick a random pebble in my path as I head to my bright red Ferrari. My next kick lands on one of my tires._ As if I am not already seeing red._ I channel my ridiculous anger towards the poor car.

I jerk the car door open and am just about to step in when I feel a small tap on my shoulder.

I whirl around and come face to face with a pair of bright brown eyes, tears shimmering at their corners.

"Hey." She whispers.

"What?" I snap, feeling my irritation come up to the surface when the subject of my annoyance stands in front of me.

She falls quiet. I peer at her, patience wearing thin.

"Now, if you don't mind, Bree is waiting for me." I bark at her, throwing out a random name from my long list of "girlfriends". She steps back at my voice, and speaks up, a renewed fire in her eyes.

"I want to thank you for not disclosing that we've already met." She clears her throat, holding her head up high now. "That's all. I'd better get back, Matt is waiting for me." She throws my words back at me, gives me a small wave, and saunters haughtily off in her black stilettos, which elongates her already slim and petite frame. I couldn't help but check out her behind, as I watch her retreating back with perplexed eyes.

This is intriguing. I frown, too surprised and confused by her sudden change in attitude and the less-than-30-minutes encounter to remember my anger. At the same time, I find myself wanting to find out more.

Who are you, Elena Gilbert?


	5. Chapter 4

**Chapter 4**

"Come on, Nana," Caroline is trying to drag me up from my bed, using my childhood nickname to get my attention. "You deserve a treat after that horrendous week!"

That is the understatement of the year. I burrow deeper under my soft comforter. Maybe if I ignore her long enough, Caroline will give up and leave me alone.

"Elena Gilbert! This is unhealthy and you know it!" Caroline says crossly. "And if you are good girlfriend you will agree to go with me to the party!"

Guess the delay and ignore tactic isn't going to work. "Caroline, you know the girlfriend card should be used with care and not thrown mindlessly around, right?" I whisper hoarsely.

Not that I really blame Caroline for her Carol-vention. Ever since I saw Damon again 3 days ago, I have not been feeling myself, escaping to my room the first chance I get. The encounter had a stronger effect on me than I thought. To top it off, I have been feeling beyond gross for pretending to like Matthew Donovan's disgusting company, as he leered at me while we went on our lunch "dates" these few days. I hate myself for having to do this. But hey, what is family for right?

My face fall at the thought of my dad. Flipping the comforter over my head, I attempt to return to my safe cocoon. But of course, the formidable Caroline Forbes will have none of it.

"Please? Pretty, pretty please?" Caroline pulls off my covers and bats her lashes at me. "I really, really like Stefan, and he is going to be there! I could use some support from my BFF."

Guilt-trip. I'm such a sucker for that.

"Fine." I sigh. "But I'm home by midnight, deal? I might just have to carve my lips to a permanent smile like that Joker character if I have to socialise with another horde of strangers for one more night."

"Yes! You'll enjoy yourself, I guarantee it!" Caroline bounces on my bed happily. "But, ew. Why would you want to look like that ugly thing? Besides, the actor is dead. It's bad luck, Nana."

I mock-roll my eyes. There's really no one like my dearest Caroline. I climb slowly out of my bed as she hopped to my walk-in wardrobe. Rows and rows of designer outfits and apparel fill the shelves, 60% of which still had tags attached to them.

"Outfits! What should we wear? Let's make Elena Gilbert a smoking hot babe tonight! This is so fun!" She shrieks as she zooms straight to my massive shoe collection, ooh-ing and ahh-ing at the Charlotte Olympias and Christian Louboutins, amongst others.

I can't help but to smile at her enthusiasm. "Caroline, what would I do without you?"

"Hmm, crash and burn." She replies cheekily. Maybe this will be a good idea after all.

* * *

I stopped to stand on my spiral staircase, enjoying the view of the crowd. The guests are all trendily dressed, mingling in small groups of 2 to 4, with colorful drinks in their hand. The party looks awesome, if I may say so myself.

"Brother! There you are. Not bad, you really pulled out all the stops, didn't you?" Stefan commented, grabbing some green cocktail off a butler's tray.

My living room had been dressed up like a classy lounge, complete with subtle colored lights, baby grand piano in the middle of the room with a pianist playing modern jazzy numbers, and butlers serving various cocktails off their trays. Comfortable couches littered the enormous space, creating sections of small seating areas for guests to settle down and hold conversation. The music is kept in the background, but still comfortably loud enough to fill any awkward silences. Not that there is any, looking at the smiles on all the guests' faces.

This is the annual Salvatore networking party, where our partners, clients, and their partners and clients come together for a get-together and of course, to expand their networks. Instead of a stuffy, corporate event, I have managed to make it into a fun and sophisticated cocktail party. Well me, and my army of caterers, of course. Invites are highly exclusive, and I have had businesses knocking on my door to work with us just so they could stand a chance be invited.

"I don't do half-assed jobs, my dear bro." I smirked, "including those for the women I hang out with." I pat the hand of my arm-candy of the night, Rose. "Don't you agree, my dear Rosie?"

She looks coyly up at me, flushing as she nodded. Stefan rolls his eyes and announced that he is going to look for his date, who had insisted on coming on her own, I heard. Why do women complain chivalry is dead when they take every chance they get to prove their independence? The female specie is really not a community one can attempt to understand.

I guide my dark-haired companion towards the bar. Rose had been hankering for my attention for almost 2 months now. What kind of gentleman am I if I don't return her affections? The need for a presentable date to my party is just a happy coincidence. I turn towards her, and am about to engage her in one of my usual conversations of pretend-interest and sexual innuendoes, when I spot her.

She glided gracefully through the hallway in a full lace 3/4 sleeved black dress, matched with blood red strappy heels and small clutch, hair in big waves framing her face. I practically salivated when I realise that the lace bodice is lined only with a small piece of black cloth underneath, covering the barest amount of skin necessary for decency. Yet, she still manage to look elegant and poised as she scans the crowd for a familiar face.

A blonde in a green satin number joins her as she starts towards the back of the room, towards... Stefan? That's when I recognised the rude blonde who refused to provide Elena's details that night. "Damon?" Rose nudges me gently, following my line of vision to find the source of my distraction. "Saw someone you need to talk to? You didn't hear a single word I said in the last 5 minutes, did you?"

I pulled my gaze away from Elena and focus on the girl in front of me. Suddenly, Rose's silk floral maxi dress, with a deep V on the neckline that showed off her cleavage, looked too trashy and revealing. Her hair was too light, and eyes too green.

"Let's join my brother over there." I steer her towards the chatting trio, and straighten my back. I'm going to show Elena Gilbert just what she is missing.

* * *

"Hi, Stefan, right? I'm Elena, Caroline's friend." I eye him warily. I am curious to find out how the young man that has captured my best friend's heart so quickly is like. Caroline tends to fall hard and fast, but so does the breaking of her heart. I have taken on the role of her protector quickly after many nights of nursing her heartbreaks, and swore to flag out any whiff of asshole-ness I detect from her suitors.

"Hey! I've heard lots about you. You're the elusive best friend." He perks, giving me a warm smile. Momentarily, he drifts and I watch his eyes light up as they land on my best friend catching up behind me. Immediately, he steps towards her and grasps her hand tightly.

"You're here! So you do live up your reputation of Miss Relentless and managed to convince Elena here to come." He winks playfully at Caroline. She blushes and slaps his arms gently. "Stop it. Elena's watching."

I grin, letting the automatic defence I usually set up for my blonde friend down a little. They look utterly in love, and I have never seen Caroline act so bashful in front of a guy. She is more of a "want it, get it" kind of girl.

"So," Caroline looks at me with eager eyes, "What do you think of this party? Awesome, right! We are going to have so much fun!"

I take in the well-decorated surroundings, impressed by the cosy ambience and intimate settings. The high ceilings, antique furniture and marble pillars and floors should be intimidating, but now, they just melted into the background. The chiffon curtains draped across most of the visible walls and pillars certainly helped to soften the room. In its raw form I would probably be astounded by the sheer size, it looks like it can fit 100 people comfortably.

I glance at the people dressed up to the nines, and feel the sound of delightful conversations around calm me down. "It certainly looks well-organised." My lips curve gently. "I'm impressed. You are the host, yes?" I direct my question to Stefan. "Who came up with the theme?"

"That will be me." A man answers in a buttery baritone behind me.


	6. Chapter 5

**Chapter 5**

_Shit_. I instantly tense as I recognise the voice. Damn the flutters in my stomach. _He was just speaking. People speak. Nothing to be nervous about._

I release a breath I didn't realise I was holding as I turn towards the direction of his voice. "Stefan is not one to brag." His face breaks into an arrogant smile as he looks at me from my face to my heels. He is a vision. I am sure he heard my deep exhalation as I struggle to maintain my composure.

"Damon. Nice to see you again." My voice is even, and unhurried, exactly how I want it to be. I silently congratulated myself for the extensive practice I had from avoiding confrontations with my father.

Inwardly, my stomach is twisted into a tight, tight knot, butterflies threatening to bring up my last meal. Nerves. I never get so nervous around men. But then again, no man is quite like Damon Salvatore. Which is why I should run away, far away from the man who looks like he can tear my heart out and chew on it. Elena Gilbert doesn't do broken hearts.

Caroline decides to speak up at this moment, scrutinizing Damon and his companion of the evening. "Oh, right, the wayward and forgetful brother." Her voice is dripping with sacarsm. "Surprised that you will find our faces familiar."

"Oh, you wound me." Faux horror decorates Damon's dace. "Your friend here has left quite an impression." He smiles his megawatt smile, and his arrogant eyes look like they can see right into my soul. I shudder at the thought.

"Miss Gilbert how nice of you to grace my humble abode."_ What's with the overtly formal attitude?_ I notice how his date's hand tighten on his arm, and felt a pang of irrational jealousy. Goodness, Elena Alexandra Gilbert, get a grip! You hardly even know the man.

Damon apparently notices the frown edging my forehead. "Why? The place not bright and cheery enough for you?" My brows shoot up from their congested position. Why does this sound so familiar?

"It's you!" I gasp. Caroline, Stefan and Damon's companion cock their head in bewilderment at my outburst. I hurriedly cover my hand over my mouth, mutters an "Excuse me, I need the powder room" and leave the conversation.

Grabbing a butler to ask for directions to the bathroom, I am beyond relieved to find it unoccupied, and lock the door behind me. Sitting on the toilet, I exhaled, trying unsuccessfully to calm my heart. It's like a battering ram in there. Somehow, finding out Damon is the mysterious intruder of my sleep that night unnerve me. This means I have his number, and vice versa. This means he is not just a passerby in my life, and we can maybe get to know each other.

_That sounds exciting!_ My heart sings.

_He stopped messaging you, and he brought another girl. He is obviously not interested._ My mind clucked disapprovingly.

Ugh. Exasperation is not a good look. I look at my cheeks, still flushing from the embarrassment of my outburst. I straighten my dress and hair, picked up and clutch, and cleared my throat. There, much better.

I glance around for Caroline and find the pretty blonde waving enthusiastically at me. She looks like she has had quite a few, noting her wobbly steps. That's fast. I head towards her, amused.

"E-leeeee-nah! Where have you been!" She pouted. "You've been gone for-evahhhh!" Stefan is holding her protectively while she steps towards me, looking apologetic and suppressing his laughter at the same time. "I couldn't stop her." He mouthed.

"Sorry for leaving my BFF high and dry." I hug her tightly. "Come on, let's get drunk!"

Caroline squeals at the "D" word, and immediately motioned to the bartender to bring on the cocktails. I tried each one, marvelling at how delicious they all are.

The prickling sensation of being watched followed me the whole night I have a vague idea who that is. I can't help to sneak a peek over to his direction. Five times, our eyes meet for 2 seconds before he goes back to laugh at her jokes. Her name is Rose, I think.

_I will not let this idiot affect me. He is just one of those good-looking rich bastards around. No reason for me to crack my well-groomed and practised demeanor to give him the time of day._ My logical mind rarely appeals to me with her cynical attitude, but this time, I know I should heed her advice.

A few, or more, definitely more, drinks later, I am giggling at the most random things. "Whee!" I cheer, "See that? Day-mon Sal-vah-toreeeeee is looking at me! Me!"

Caroline giggled with me, obviously not catching my gleeful comment. "Whee!" A couple of other guests look at us in amusement, wisely choosing to not butt into our own private party. I guess we are lucky that the bar is a distance from the main seating area.

Suddenly, my world rotates dangerously on its own axis, and I stumble into the seat right next to me. "Whoops. And that, my dears, signals the end of the night!" I pull myself to my feet, and gestured to Caroline that I'm leaving.

"Buh-bye Nana!" She grins at me, clutching Stefan's arm tightly. "My cute little boy here will take care of me!"

Stefan blushes, and nods his consent. He has been nothing but dependable tonight, looking out for Caroline and myself as we made the most of the cocktails and the party. He also managed somehow to introduce me to some people of importance, despite Caroline's and my obvious agenda Mission Have Fun and Get Drunk. He has definitely won me over.

"Are you good on your own though?" Stefan look at me with concern.

"Nah, don't worry about me. I'll just grab a cab." I gave a small wave, and turn to walk out of the hallway. The night turned out not too bad at all. I smile at myself, feeling a little triumphant that Damon hasn't taken his eyes off me the whole evening. Where is he now? I wondered. _Maybe with that date of his, you know, the one he chose to bring?_ My mind chatises.

I roll my eyes, and sit on the steps of the porch, waiting for the doormen to call me a cab. I glance at my watch. It's already 2AM. So much for being home by midnight. Placing my head on my knees, I shivered as the cool night breeze blows. I hug my knees closer to my body. If only romance is the only problem I face in my life, a life that many think is blessed and worry-free. Sighing, I look into the distance, lost in my thoughts.

I feel, rather than see him sit beside me quietly, drapping his jacket over my shoulders. "Who do we have here?" I close my eyes as his smooth, deep voice flows and envelopes me. He sounds so much more gentle than before.

"Hey" I turn my head to face him. "Great party."

"You should only expect the best from me." His smile is cheeky, and his comment is devoid of the arrogance that I anticipated. His eyes gleam in the dim lights. I feel his warmth, and fights the urge to lean towards him. Sometimes, a perfect stranger is who I need. Someone who doesn't know what i have to make myself do. Someone who can hold me and not judge me for the shit I force myself to swallow.

I shake my head almost imperceptibly, and stand up, shrugging the jacket off of me. "I... I need to go. I er... I've had too much to drink." I muttered. "Excuse me."

I stagger as I descend from the steps, only to be held by a strong pair of arms. His arms. "Come, let me send you home."

I start to protest, but words seem to leave my lips when I look up at him, his face just centimetres from mine. I nodded weakly, and let him lead me to his Ferarri.

He cautiously helps me into the passenger seat and straps me in. "Mmm. A gentleman." A cheeky smile adorns my face. The alcohol decides to make me bolder at this moment. He pauses, gauging my mood, and mirrors my expression, with a glint in his ocean blue eyes. "That would be my impeccable upbringing."

We ride in his car in comfortable silence. I sneak a glance at him, strong hands on the steering wheel, concentrating on the road.

"Why are you so sad, Elena?" I must have drifted away unknowingly; his question startles me.

"Sad?" I fiddle my fingers, "What makes you think that?"

"Your look, at the steps. You confuse me, you know."

I find myself holding my breath for the second time tonight. I decide that distraction is in order. "I thought you can charm the pants off any woman. So much for your reputation, Damon." I try to sound coy, to mask my uneasiness with flirting.

He falls quiet. The remaining distance is punctuated only by the smooth sound of his engine. I provide him with the roundabout directions to my apartment, unwilling to leave his company even with his stony silence.

"Thank you", I shift to remove my seatbelt, as he pulls up at the entrance of my Upper West Side apartment. He smiles stiffly, and exits the car to open the door on my side.

"You're good to head up on your own?" He steadies me, making sure that I am sober enough to walk.

"Yup, no problem." I try a bright smile but bring up a half grimace instead. What a miserable attempt.

Damon chuckles. He brings his hands to my chin, and strokes it gently. "What is Matthew Donovan to you?"

My brows fly up to my hairline, surprised at that question. "Erm, a... friend?"

"Good, which means I don't have to feel guilty doing this."

The next thing I know, I am wrapped up in his arms. He places his right hand on the small of my back, his left caresses my chin, and lean into me. His lips captured mine as he kisses me softly, moving about gently, cautiously.

_Holy..._

My eyes close on their own accord. I let myself let go and kiss him back. My mind is numb. I go breathless. I sense what feels like electric shocks all over me.

Then, as sudden as it started, it's over. I open my eyes in shock, and watch him already sauntering back to his car, his signature arrogant smile in place. "You owe me a kiss anyway, Elena Alexandra Gilbert."

I stand frozen on the spot as he drives away. What?


	7. Chapter 6

**Chapter 6**

I whistle a happy tune as my car roars away from Elena's place. If I am not driving, I will be jumping off my seat in excitement.

Score! The kiss is way, way more satisfying than I thought it will be. Her lips are so soft. A smile ghosted my face as I recall the look on her face when I left.

One moment. At that one moment I am a free man. I can answer the currents that pulsed through me ever since I laid my eyes on her tonight. If only I can have that pleasure more often.

I unlock my cellphone and type out a message.

To Elena Gilbert: _Goodnight, silly, exasperating woman._ I grin to the lited screen.

It's now 3.30AM, too late for anyone to be awake, and safe from the prying eyes of the paparazzi. Even relentless photographers and reporters need to sleep. I pull up at the foyer and wave for Edgar to park the car.

I ascend the short flight of steps to the Brooklyn apartment. The place exudes an artistic flair large colorful paintings decorate the walls, and eclectic throws lie on the floors.

Gently, I open a door on my right and enter the room, careful not to wake her up. Closing the door behind me, I hear her shuffle.

"Hey, you're here. Late night?"

I sigh quietly and walk to the side of the bed, caressing her hair.

"Yes, my dear. Why are you awake? I told you never to wait up for me."

"I want to see you come back to me. No matter where you go, you are supposed to come back to me, remember?"

I nod and tuck her into the comforter. "That's why I come by, every night." I give her a peck on her forehead. "Now, go back to bed."

"Stay with me. I missed you."

I sweep her fringe aside gently. "Okay. Only for you."

* * *

From Damon Salvatore: _Goodnight, you silly, exasperating woman._

Silly? Exasperating? I pride myself as a sharp, discerning woman who knows what she wants and go for it, independent of anything and anyone. (Well, most of the time anyway.) But not exasperating and certainly not silly!

_Maybe your game face is the one putting him off._ My mind says disapprovingly. _But he saw right through you! Why else would he kiss you?_ My heart winks.

Ugh. I glare at the message accusingly and tries to erase the incident that happened 3 nights ago. I must have stared at that offensive sentence more than a dozen times in the last few days. I refuse to reply, indignant as I am. Why should I waste time and energy of that idiot? He clearly does not know me at all. _But why has he gotten under my skin so quickly?_

"Elena? E-le-na?" Matt tsks at me in irritation. "Excuse me? Do you know how rude it is to ignore someone when he is speaking to you? How dare you!"

"Erm, sorry... sorry." I mutter, trying to make myself smaller under his scrutiny. "I'm just... worried. About work. Yes. Work." I attempt at a coy grin to get myself out of the situation.

"I hope you acknowledge how lucky you are to be seated at the same table as me, Gilbert." Matt leers at me haughtily. "There are plenty of girls_ begging_ to be near this fine specimen." He gestures to himself. "Though not all are as hot as you." He winks.

I suppress my gag reflex and paste a flirty smile on my face. "You mean it's not my charm that got you here? The horror!"

"My darlin', sometimes even charm and good looks are not enough." He trails his index finger on my arm suggestively. "How far are you willing to go?"

I visibly shudder. This man is revolting.

I dodge quickly, pretending to be cheeky. Matt furrows his brows and drops his hand, as if wondering why anyone will want to avoid his touch.

"So!" I try to change the topic with my loud voice. "How's the bidding coming along? Have you decided on the lucky contender for the construction on that prime piece of land in Murray Hill?" I flutter my lashes, channeling my inner Caroline. "I simply love that neighborhood!"

"Oh come on, don't be stupid. Why would I reveal confidential information to you, oh Golden Princess of G Enterprises? Especially since yours is one of those competing for the very spot." He gets up from his side of the booth seat and snuggles next to me suddenly. I try not to cringe. "But I can very easily be persuaded to show some favoritism, if you know what I mean..." He snakes his arm around my waist.

I laugh as I push him away gently, "Good things come to those who wait." I let my hands linger longer than necessary to soften the blow.

"Elena," Matt sneers, raising his voice with every passing second, "You know I am not a patient man. I am willing to give you a small percentage of my precious time only because of my Dad's relationship with your father."

"Matt, stop it. People are starting to stare." I whimper fearfully. The dangerous glint in his eyes is giving me the creeps and he looks positively violent. Just when I was contemplating my quick exit, he grabs my arm, pulls it forcefully to his chest, and throws out, "You think you can tease me with your little games. But I can't promise how long my attention span is going to be."

He flings my arm aside and stomps out of the restaurant. I glared at his retreating back, while trying to avoid eye contact with the other patrons. A waiter hurries over to check on me, clearly having witnessed the whole debacle. "Just put the meal on my tab. Elena Gilbert." I dismiss him with a wave of my hand.

Walking as quickly as possible towards the Ladies, I frantically rearranging my hair so that it falls around me and covers the sides of my face. _Why am I always subjecting myself to such humiliation?_ I am Elena Gilbert. I am supposedly the woman leading the entire sales and marketing department of my father's multi-million construction business. Everyone knows I am almost covering entirely for that useless General Manager called Tyler Lockwood, whom my father only hired to "keep my ego and sense of entitlement" in check. "People need to know that just because you are my daughter, you are automatically the heir to my empire. I need to look impartial."

More like he enjoys sending me on despicable missions like this. I lean my back against the cubicle door and slide to the ground, biting my lips and willing myself not to cry. I hate this. I really hate this. This is not how I envision myself at 25. I am supposed to grow up, decide if i want to have kids and start a family, grow old. These are the ideals and dreams my mum taught me.

_Mum... I miss you so much..._ I break down, sobbing to myself, curled into a ball, in a public restroom in the middle of lunch. All by myself.


	8. Chapter 7

Thanks for reading this story so far. I am not really a fan of A/N so this is going to be short. Just wanted to apologies for the slow updates. Was planning to update this every 4 to 5 days, but real life got in the way. Plus I have writer's block. Updates might be slower for a bit, but I promise updates will be faster once life gets calmer, around end July! Enjoy this chapter, and feel free to tell me what you think. :)

* * *

**Chapter 7**

After taking almost half an hour to refresh my makeup, I manage to fix the smeared mascara and eyeliner. Now I look like my usual confident, respected self, instead of the emotional wreck I am. Smoothing my hair, I grab my files and start to head to the monthly department meeting.

At the lobby, I nod at Bonita, my colleague and fastest rising star of G Enterprises.

Bonita Bennett is the kind of girl that seems harmless enough; but she seems to be able to rub everyone the wrong way with her "accidental-international" snide remarks. Her perpetual sweet smile, on the other hand, makes you wonder if you are just reading too much into her words. I have no complaints about her capability though. She is the best worker one can hope for she singlehandedly revamped our production system and schedule, and rose to Head of Production in her short stint of 3 years here.

There had been rumours of her being a worthy contender for the General Manager role, alongside myself, if that Tyler Lockwood is being ousted from the job. So I have always maintained a wary attitude towards her.

"Elena." Bonita greets me. "Didn't get a good night sleep? Your eyes look a little puffy."

I mutter a noise of agreement and give her a smile as I look ahead, as my mind starts to wander, hoping this will discourage her from chatting with me. I hate small talks.

I drift to the messages I exchanged with Damon after calming myself down.

Me: Your exasperation could be nothing more than your inability to decipher me like your usual conquests.

(To my surprise, his response was almost immediate.)

Damon Salvatore: This sounds like an invitation. Are you offering me a chance to find out more? ;)

Me: Do you have to read too much between the lines?

Damon Salvatore: Can't pass up an open invitation. :) Challenge accepted. Dinner tonight?.7PM. Per Se.

I stopped replying at that point. I have no idea why I started replying at all. Maybe it is just easier to feel comfortable when someone doesn't have a clue how I really live. Even Caroline gets on my nerves with her sympathetic looks sometimes. And he makes me smile. Win-win.

"...right? What do you think?" Bonita looks questioningly at me.

"Hmm?" I jolt out of my reverie. "Sorry, you were saying?"

"You are really out of it, aren't you?" Bonita laughed. "I said 'Do you think what Claire wore today is right? That sheer blouse thingy?"

"Oh." Small talk it is then. "Erm. Not really my style."

"Oh?" Bonita curls her lips in a really unflattering smirk. Damn, I need to stop being bitchy. Yes, it's just in my mind, but still. "Well, I would try it. If you are really stylish, _anything_ you wear will be your style." She flips her hair and looks at my outfit condescendingly.

There it is. She looks at me pointedly, her smirk transforming into a sweet smile. I have to bite the inside of my cheek to stop my eyes from rolling. I give her a polite smile and steps out of the lift.

Shit. What should I wear tonight? Do I have time to change? I look down at my outfit and sigh. Now I feel even worse about my outfit, thanks to lil' ol' _Bonnie_ . I mentally calculates if I can drop by 5th Avenue after work and still make it to dinner, as the meeting commences.

"The D & M Inc is going to be our biggest project this year. We have to get it." My dad's voice has always been demanding, but when he is determined to get something, his commanding tone gets downright scary. "Bonita, did you manage to find out what our other competitors are doing? Mark down the cost as much as you can. I don't care if the profit margin is marginal, once we get this, a lot of doors are going to be opened."

"Oh, Mr G, I told you, just call me Bonnie." Bonita drawls. "And you know I will do anything I can to get this job. Just leave it in my hands."

My father grunts approvingly, and I feel his heated gaze on me next. I sober my thoughts and sit up straighter.

"And Elena? I trust you have things under control in your _capable_ hands?" Sarcasm is dripping liberally with his every word, and I have to hold my fists tightly on my lap to avoid causing a scene in front of the whole senior management.

"Everything's going fine, Mr Gilbert." I address him in an overly formal manner, knowing that will piss him off right away. I smile inwardly at this petty victory. "I have been in contact with Mr Donovan, and I should be able to find out more concrete information from him."

No one in the senior management team knows about the slimy things Grayson sends my way. No one is supposed to know, anyway. This is the reason why I can still hold my head high in the office, without caring if I have to feel ashamed or guilt at the lengths I go for some of the company's bigger projects.

"Don't worry Mr G, Elena is the best." Bonita speaks up suddenly. "All of us know we can count on her." I frown at her knowing smirk. Suddenly, I feel exposed. Does she know something?

"Good. Keep me in the loop. I don't want to clear up any of your mess if this falls through." My father says, standing up and dusting some invisible lint off his jacket. "And just so you know, if I don't get what I want, I can't promise the company's headcount won't drop. It will _really_ be regrettable if I have to lose any of you." He gives a chilling smile and looks around, his eyes falling on me again. "That includes you, Elena."

He throws that out and sauntered off. I shoot daggers at his back. With a father like this, who needs enemies?

* * *

I whistle and do a little jig in my office as I drop a note to my secretary for dinner reservations. I knew it is just a matter of time before Elena caves. I smirk as I drum up ways I'm going to mindfuck her tonight. She's special, challenging, and Damon Salvatore never backs down from a challenge. Have to keep my reputation intact.

"Wow, someone's in a good mood." Alaric strolls in and sits himself at the corner of my desk. "Whose panties are you getting into tonight?"

I raise my brow at him. "Have you ever heard of knocking? And I happen to have 2 well-functioning, very comfortable chairs, and a whole set of leather sofa suited even for those with piles. Care to put them to good use and get your ass off my desk?" My tone carries just a small hint of threat.

"Aw, come on. _'Treat this place like a home.'_ That's what you said, remember?" Alaric fakes a pout. "How can you go back on your promises like this?"

"Yea, I don't place my well-toned ass on the furniture I work on." I point my finger at him and gesture to one of the chairs, like a father disciplining a naughty child. "Sit down like a civilised person. Now, to what do I owe your delightful company?" I ask dismissively, as I go through some emails.

Alaric grudgingly sinks into a chair, and started playing with a Rubix cube from my desk. "Just wondering what is this rumour I heard about you and a certain Elena Gilbert from G Enterprises."

I look up at him. "Eh? How do you know about that?"

"So it's true?" Alaric shoots up from his chair. "Are you out of your friggin' mind? Do not tell me you have no idea what this means!"

"Relax, my man. She... piqued my interest." I smile to myself, thinking back to the kiss. "Just a little mystery that I need to unveil. I promise to give her back to her precious Daddy in one piece once I'm done."

"You know that is not what I am talking about. Never shit where you eat, ever heard of this wonderful saying?" Alaric glares at me. This is one of the very rare times my dear friend wears a menacing look on his face. As head of Public Relations, wearing a smile on his face is practically in his job scope.

"You are looking way too seriously into this." I try to reassure him. Not the best time to incur the wrath of my best friend, not when I am formulating a plan to decipher a certain Gilbert. I'm sure my initial obsession with her is just because of the shroud of mystery she covered herself in.

"I swear one day you will be the death of me." Alaric looks at me accusingly. "Living vicariously through you have brought so much drama in my life I think I will never need to watch any soap operas of my own _ever_."

"Calm down. Everything will be fine." I pat his shoulder in what I hope is a calming manner. "Now, I have a date to get ready for in 30 minutes, and I really need to clear my emails before then. Do you mind?"

"This is so going to bite you in the ass." Alaric mutters as he strides to my door. I pretend not to hear him and go back to my emails. What is the worst that can happen? No one knows about me and _her_, _she_ doesn't know about Elena and I. I've always had my fun. This time will not be different.

This is only going to be some fun and excitement to spruce up my list of conquests. Nothing more. I absent mindedly drifts back to the networking party, and feel a tug in my chest. Clearly my heart does not agree.


	9. Chapter 8

**Sorry to keep you guys waiting! Extra long chapter to make up for it. :)**

**Chapter 8**

"...and that's it? Come on, there has got to be more than that!" Caroline shrieks into the receiver. I hold the phone slightly away to avoid possible deafness.

"Do you want to go up another octave? I think there are some dogs in our 10-mile radius which are not barking at the frequency of your voice yet." Rolling my eyes, I go back to painting the rest of my toes.

"But there's just so much chemistry! Stefan and I talk about that all the time." Caroline says defensively. "Like he has never seen his brother look so excited over a date before! And... and he didn't even invite you to his bed immediately after. That's progress and commitment right there, Nana!"

Caroline has been rooting for us ever since she heard about what happened after the party, and his proposition of the dinner date. I clearly recall her displaying her claws at the infuriating, albeit gorgeous man who didn't even remember our names. How she went from zero to full-fledged fangirl, I have no idea. Stefan must have a stronger influence on her than I thought. I vaguely wonder what back stories Stefan has fed her that I don't know.

Pushing away the little twinge of irritation at being out of the loop, I sigh dramatically into the phone. "Care, you know his reputation. And you know what I have been doing. Surely you can put two and two together and know nothing can come out of this. He is just a distraction, some spice to add into my pathetic life." I suddenly feel like I am convincing myself more than her.

The lovely date did nothing to dispel the notion of him possibly being something more. We talked about the random-est of stuff, from embarrassing first dates to the craziest thing we did in high school. It was way more enjoyable than I thought it would be. For that night, I completely forgot everything screwed up about myself. I applaud myself for the good choice of distraction.

The night was perfect; he came to pick me up like the gentleman he is in his fancy red Ferrari, waltzed into Per Se to his "regular booth" with me in tow. I remember wondering if he regularly brings his conquest to the popular restaurant.

Conversation flowed surprisingly smoothly. There was his usual sexual innuendos and snarkiness, of course, but he seemed genuinely sincere about wanting to know me. I found myself filing his expressions away; he just looked so boyishly pretty with his eyes shining with interest. I have to give it to him, he really knows how to make a girl blush and feel special.

* * *

"Please, you _know_ Daenerys would be better off agreeing to Xaro's proposal!" Damon is gesturing wildly with his hands. "It was just a business deal! He will fund her return, she will be his arm candy. Perfect arrangement."

I look at him disapprovingly. "She was clearly still so in love with Khal Drogo! How do you expect her to just abandon the memory of the moon of her life and her unborn child? Love is more than just practicality." I can't believe we are having such a passionate debate on Game of Thrones.

The conversation veers sideways with just one smoldering look from Damon. He raises his eyebrow at me, studying me with apparent new found appreciation. "So, a romantic, aren't you? What sort of ideals have you already imagined and pegged onto your Prince Charming?" His lips curl into a seductive smile. "What sort of qualities have you noted down in your little black book?"

I shift in my seat and try to focus on something else. Despite my best efforts, I feel my face getting hot. "What little black book? I... I just have some expectations on my other half! A girl like me certainly can choose, can't she?"

Right on cue, my phone light up with Matt's smiling photo. He has insisted that I save his photo along with his number, so that I "will never forget such a pretty face". I grab it in a hurry and switch off the ringtone.

I wonder if Damon saw the name pop up on my screen. Peering at him, I sense his wall of detachment come up. _Guess so._

"Yes, she certainly can." He replies softly.

* * *

Honestly, I expected the night to end in a "wham, bam, thank you mdm" manner, but instead of "your place or mine", he just gave me a chaste kiss on the forehead and left me alone at my door. I can't help but feel disappointed. I wonder momentarily if that means I am just not attractive enough to be marked on his bedpost. He can't possibly be so bothered by Matt, can he? He certainly acted normal enough after that... incident, perhaps with a notch less enthusiasm.

Caroline's voice turns small and gentle. "I just want someone to make you happy." I close my eyes and try to ignore the image of her pitying looks that my mind has conjured. "Maybe once Grayson knows someone cares about you, someone like Damon Salvatore, then you can stop doing that for him."

_Fat hope._ My mind screams at me. _That is the only thing he thinks you are good for. What makes you think he will let you off the hook? He's probably already planning to ship you away to the next mercenary capitalist who can add glory to the company by being his son-in-law!_

"It's not so easy." I shake my head, although I will not let anyone, not even Caroline, see the helplessness on my face. "I lost the power to fight for myself since a year ago."

I hastily ended the conversation with some lame excuse, annoyed at how fast the conversation spiraled. Care didn't let me go before I promise to spend tomorrow with her, of course. Between Damon, Matt and my job, I really have been neglecting her.

Funny how just 2 guys, a date, and a best friend can make my life so complicated.

* * *

Funny how just 2 girls, a date, and a best friend can make my life so complicated.

I muse over my third glass of scotch. I can still picture the way she looked vividly. Perhaps Per Se was too high profile a place to bring her to, but the possibility of paparazzi strangely didn't cross my mind. I just wanted to bring her to my favorite restaurant, I realise.

"Wow, alcohol at 7 in the morning. That's early, even for you." Stefan comments as he makes his way to the coffee machine, pulling 2 mugs from the cabinet along the way.

"Barbie didn't do the walk of shame before you woke up? Damn, she is a keeper." I quip. Teasing my little brother is a bad habit I have no intention of kicking.

"Har har." Giving his typical Stefan-ish dry laughter, he turns around and studies me. "So, what's up? The company's doing well, which is obvious from the numbers I spied from Wall Street, your loved ones, a.k.a. Alaric and myself are alive and well, the last I heard anyway. You have girls surrounding you every single night. What is so tough in your life, man."

"Oh come on, it's just a teensy little glass of scotch. I'm sure it's 5PM somewhere." I conveniently leave out the other glasses I've already consumed, both consisting of 2 very generous fingers of the amber poison.

"Well, suit yourself. I know we are not big on that hugs and kisses deal, but you know I'm here when you need me." Stefan mock salutes me with one of his coffee mugs, and makes his way out of the kitchen.

"Hey! I distinctly remember saying "none of that chick flick shit" when I agreed to take you into my massively beautiful house!" I shout after him. That might be just slightly childish of me, but hey, I'm inebriated, I'm allowed.

As I slide my index finger absently on the edge of my phone, I consider if I should keep in contact with Elena. The dinner has been nothing but perfect, marred only by that call she got from Matt. She looked so panicked. No one looks that panicked when they get a call from a friend on a date. I have been trying to wiggle my way around our social circle, to see if I can get any inkling of the relationship between Matt and Elena, but I've got zip. This bothers more way more than I care to admit.

Elena. Such a vibrant, intelligent young woman, who seemed confident of what she wants and is actively working towards it. Her determination and knowledge earned my respect in that short amount of time we spent together. I am not easily impressed, and yet, I am. By her.

Ah, screw it! I fling my phone aside and stride to the bar, refilling my glass with another round. I haven't had the need to put so much effort on a girl since... Ugh.

Snatching my phone up from the carpeted corner, I type 2 simple words, before capping my tumbler of the fine whisky, and heading upstairs.

**Me: Lunch tomorrow?**

* * *

Clutching Page Six tightly in my hands, I struggle to keep my temper in check and not just flip the whole damn table over. I opt to sweep my plate of scrambled eggs onto the floor instead.

What the hell is happening? Of all people, he chose _her_? And right under my nose? Even heading to Per Se, his favorite restaurant. He must have been trying hard to impress her.

"Ugh!" How dare he. How _dare_ he? I have no qualms tolerating his infidelity with those nameless models and sluts. But_ her_?

I breathe heavily through my mouth. I must return to my carefully built fortress of zen. Only peace will allow me to plan my strategy properly. I cannot let him slip through my fingers. I just.. can't. He must come back to me. He is supposed to _always_ come back to me.

I tear the flimsy recycled papers into pieces, refusing to let the sneakily taken photo of Damon and a certain brunette stare back at me any longer.

"No. You will not take what's mine." I fume. "Never!"


	10. Chapter 9

I hum to myself as I leisurely browse the Internet for the latest movies showing in the theatres.

Life is _good_.

Out of the corner of my eye, I glance at the balled up sheet of newspaper, 2 months old now. Despite the streak of anger that went through my veins when I lay my eyes on it, I can still feel a distinct surge of warmth.

My disregard for privacy on my first dinner out with Elena earned me a full page spread on Page Six. Not that it is unexpected. I just assumed that the paparazzi would be meaner than simply painting the page with the title "Damon's advancement on Little Miss Mysterious" in a huge-ass font. Seemed like they were intrigued with the proper and graceful Miss Gilbert like I was, and instantly picked up the difference in the way she carried herself, as compared to my other conquests.

Which is partly true, since she is not my conquest. Not really. Since that night, we have been meeting up almost every other day, just enjoying each other's company. She looked delicious every time, with her jackets and little shift dresses she wore to work, or her loose shirts and short shorts on the weekends.

So why have I not made her mine yet? This is a question I ponder before I sleep, every night.

I guess I have been so worried about screwing this up that I just didn't want to complicate things in any way. Not that I'll ever admit it, of course. I am simply contented with Elena's company, and the many, many things we talk about every time we meet.

And then there's _her_. I feel my brows crinkling in frustration and guilt. She didn't act like anything is out of the ordinary, of course. But I'm sure she'd noticed the paps' lack of updates on the notches on my bedposts, and their obsession with noting Elena and my every move. Their headlines have changed to "New York's golden boy smitten with Princess of G Enterprises" or "Playboy tamed – is Delena end game?"

I have been brushing her questioning gazes and hints aside – how do I explain something I do not even fully comprehend, myself? Her expressions of hurt, neglect, and occasionally jealousy and angst of course did not go unnoticed. But I have the confidence that she would not and could not go after Elena.

I have to balance this delicate situation as best as I could. Losing either side is not going to happen.

Forcibly pushing my unsavoury thoughts aside, I click the "Purchase" button on the website, and pressed the speed-dial on my phone.

"Hey babe, I got the tickets. I'll see you at 7PM sharp tonight – I will not accept any bullshit about working late a'right?"

* * *

I smile to myself as I hear his deep baritone on my voicemail. I mentally snuggled into the comfort of his voice, so that I can block the thoroughly god-awful week I had.

Everybody is on my case recently. Tech services gave me grief for "the lack of consultation when the new websites are implemented"; Finance chided me for not being informed of the new policies that required approval for any expenses above $20,000; my father has been exceptionally unkind and clipped in his little interaction with me.

I am just about to explode.

Other than my trusty assistant, an unexpected ally seemed to be helping me out as well. Bonnie. She has been there to resolve issues for me, many of which do not even directly concern her.

"Just happy to help out a colleague" she says. At this point, any help is so greatly appreciated I just embrace it without any further thought. Despite the slight irritation I have always had with her, she has been a godsend.

I breathe out a sigh at the mountain of paperwork that simply refuses to diminish despite how hard I plow through them. I collapse heavily on my chair. Crunch time.

"Gilbert!" A familiar voice sounded from beyond the mountain. I cannot even see past them. "Wow, talk about being buried in work. How do you get yourself so much paperwork?"

"Hey Bonnie," I greeted meekly. Need to save some energy to dig into the work.

_And for the movie date later!_ Haha. My mind likes to joke. I'll be lucky if I stay awake throughout the show.

"Anyway," Bonnie peered at me above the pile of papers. "I brought you some Earl Grey. Twinings! Your fave, right?"

I beamed at her and accepted the mug of hot, calming goodness gratefully. "What will I do without you, Bennett?"

She waved my thanks aside, and propped herself on the arm of a small loveseat I have in my room for visitors. Playing with the corner of one of the cushions, she watches me sip the hot tea, looking deep in thought.

"So tell me – how does the fastest rising star of G Enterprises find time to bring me tea and lounge in my office? Are we overstaffed?" I joke.

"Nah, just need some help from a girlfriend." Bonnie looks at me with a twinkle in her eye. Somehow, I have a bad feeling about this.

"What's up?" I feign ignorance.

_Not the Gala. Not the Gala. Not the Gala. _My mind chants.

"Well, I was hoping I can convince you to go to the Gala with me tonight."

I groan inwardly. I have been staying away from Matthew since I started hanging out so frequently with Damon. Yes, _hanging out_, since there has been next to zero intimate interactions between us. The tension is there, but neither of us acted on it.

Or he almost did, but somehow always manage to avoid any actual cosying up in the last minute. So much so that sometimes I feel that I've been "friendzoned". And I thought that's a term for guys only.

Instead of half-heartedly seducing Matt, I decided to target his secretary instead. Thanks to my ability to channel my inner Caroline, I have managed to be _girlfriends_ with Anna. Just 2 more tiresome high tea sessions, and I should be able to get everything I need.

This all but rendered any interactions with Matt unnecessary. Hence the avoidance.

But of course, tonight is the Donovan appreciation Gala, which is simply an excuse for the wealthy and powerful to gather, complete with expensive Champagne and the pretense of donation to Charity. And the "appreciation" bit? Just the official reason that the Donovans quote so that they can display their connections in the city.

"I thought Lockwood's supposed to be your date," I pretend to be entirely engross in reading yet another advertising contract with some trade magazine. "Not very gentlemanly for him to ditch at such a last minute, right? Plus I thought he lives for free expensive Champagne and the chance to wear his many Hugo Boss suits." _As opposed to actually working and bringing some value to justify his obscenely huge paycheck. _I silently add.

"Yes, he was supposed to go. But he decided to bring his own date last minute. Some bimbo he wanted to impress, apparently." Bonnie looks at me with wide eyes. "And I really don't want to go alone. Help a girl out? Please?"

I curse inwardly. After accepting so much of her help, I practically have no choice in this matter. At least I might be able to strengthen the friendship with Anna enough to get what I need from her.

Swallowing my disappointment at having to miss movie night with Damon, and bracing myself for the inevitable leering and lewd remarks from Matt later this evening, I plaster a huge smile on my face.

" Sure! What are girlfriends for?"

Little do I know, these are the 6 words I will regret for the next 2 years.


End file.
